Alternative donor-acceptor stacks from crown ethers and naphthalene diimide derivatives: Rapid, selective formation from solution and solid state grinding

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2078-2079

  Koshkakaryan, Gayane ^a   Klivansky, Liana M ^a   Cao, Dennis ^a   Snauko, Marian ^a   Teat, Simon J ^a   Struppe, Jochem O ^b   Liu, Yi ^a  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^b BRUKER BIOSPIN CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEGREE OF ORGANIZATION; DONOR-ACCEPTOR; ELECTROACTIVE; ELECTRON-DEFICIENT; ELECTRON-RICH; HIGH YIELD; HOST-GUEST SYSTEM; MACROCYCLIC; MECHANICAL GRINDING; NAPHTHALENE DIIMIDE; POLYCRYSTALLINE AGGREGATES; POWDER X RAY DIFFRACTION; SELECTIVE FORMATION; SOLID-STATE NMR SPECTROSCOPY; SOLID-STATE STRUCTURES;

ADA (PROGRAMMING LANGUAGE); CROWN ETHERS; ETHERS; GRINDING (COMMINUTION); GRINDING (MACHINING); LIGANDS; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; SINGLE CRYSTALS; X RAY DIFFRACTION ANALYSIS;

SOLID SOLUTIONS;

AROMATIC CARBOXYLIC ACID; CROWN ETHER; MACROGOL; NAPHTHALENE DERIVATIVE; NAPHTHALENE DIIMIDE; UNCLASSIFIED DRUG;

ALTERNATIVE ENERGY; ARTICLE; BINDING AFFINITY; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ENVIRONMENT; CHEMICAL STRUCTURE; CRYSTALLIZATION; DONOR SELECTION; ENERGY TRANSFER; GRINDING; HYDROGEN BOND; LIQUID CRYSTAL; MECHANOTRANSDUCTION; MOLECULAR INTERACTION; NITROGEN NUCLEAR MAGNETIC RESONANCE; POLARIZATION; POWDER DIFFRACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 67849110373     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809088v     Document Type: Article

References (36)

1. Forrest, S. R.; Thompson, M. E. Chem. Rev. 2007, 107, 923-925.
2. Schwoerer, M.; Wolf, H. C. Organic Molecular Solids; Wiley-VCH: Weinheim, 2007.
3. (a) McConnell, H. M.; Hoffman, B. M.; Metzger, R. M. Proc. Natl. Acad. Sci. U.S.A. 1965, 53, 46-50.
4. (b) Torrance, J. B.; Vazquez, J. E.; Mayerle, J. J.; Lee, V. Y. Phys. Rev. Lett. 1981, 46, 253-257.
5. (a) Okamoto, H.; Mitani, T.; Tokura, Y.; Koshihara, S.; Komatsu, T.; Iwasa, Y.; Koda, T.; Saito, G. Phys. Rev.B 1991, 43, 8224-8232.
6. (b) Collet, E.; et al. Science 2003, 300, 612-615.
7. (c) Horiuchi, S.; Tokura, Y. Nat. Mater. 2008, 7, 357-366.
8. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
9. (b) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 3, 651-659.
10. (c) Griffiths, K. E.; Stoddart, J. F. Pure. Appl. Chem. 2008, 80, 485-506.
11. (a) Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303-310.
12. (b) Gabriel, G. J.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 15174-15175.
13. (c) Gabriel, G. J.; Sorey, S.; Iverson, B. L. J. Am. Chem. Soc. 2005, 127, 2637-2640.
14. Zhou, Q.-Z.; Jiang, X.-K.; Shao, X.-B.; Chen, G.-J.; Jia, M.-X.; Li, Z.-T. Ore. Lett. 2003, 5, 1955-1958.
15. (a) Ghosh, S.; Ramakrishnan, S. Angew. Chem., Int. Ed. 2004, 43, 3265-3268.
16. (b) Ghosh, S.; Ramakrisham, S. Angew. Chem., Int. Ed. 2005, 44, 5441-5447.
17. (a) Patrick, C. R.; Prosser, G. S. Nature 1960, 187, 1021-1021.
18. Hamilton, D. G.; Lynch, D. E.; Byriel, K. A.; Kennard, C. H. L. Aust. J. Chem. 1997, 50, 439-446.
19. (a) Percec, V.; et al. Nature 2002, 419, 384-387.
20. (b) Park, L. Y.; Hamilton, D. G.; McGehee, E. A.; McMenimen, K. A. J. Am. Chem. Soc. 2003, 125, 10586-10590.
21. (c) Reczek, J. J.; Villazor, K. R.; Lynch, V.; Swager, T. M.; Iverson, B. L. J. Am. Chem. Soc. 2006, 128, 7995-8002.
22. Pisula, W.; Kastler, M.; Wasserfallen, D.; Robertson, J. W. F.; Nolde, F.; Kohl, C.; Mullen, K. Angew. Chem., Int. Ed. 2006, 45, 819-823.
23. (a) Stoddart, J. F. Pure. Appl. Chem. 1988, 60, 467-472.
24. (b) Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1547-1550.
25. (c) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem.-Eur. J. 1998, 4, 608-617.
26. Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem., Int. Ed. 2004, 43, 1959-1962.
27. (a) Ortholand, J.-Y.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1394-1395.
28. (b) Asakawa, M.; Dehaen, W.; L'abbe, G.; Menzer, S.; Nouwen, J.; Raymo, F. M.; Stoddart, J. F.; Williams, D. J. J. Org. Chem. 1996, 61, 9591-9595.
29. Crystals suitable for X-ray single crystal analysis were grown by a heterogeneous layer diffusion method. It is noteworthy that although the stack required a 1:2 ratio of two components, the assembly proved to be effective starting from exceedingly biased concentrations. See SI for crystallographic data and crystal growing conditions.
30. The electrostatic potential (ESP) plots of 2a-2d revealed (see SI) that 2c had the most positive π clouds, while 2d had the least.
31. See SI for a detailed description of the competition experiment.
32. The presence of solvent can significantly shorten the grinding time. A ball mill apparatus worked equally efficiently at mortar-and-pestle grinding.
33. The purple color is a good indication for the ADA stack formation, which is absent when mixtures of 1 and 2c-h are ground.
34. (a) Orita, A.; Okano, J.; Tawa, Y.; Liang, L.; Otera, J. Angew. Chem., Int. Ed. 2004, 43, 3724-3728.
35. (b) Kihara, N.; Hinoue, K.; Takata, T. Macromolecules 2005, 38, 223-226.
36. (c) Hsueh, S.-Y.; Cheng, K.-W.; Lai, C-C.; Chiu, S.-H. Angew. Chem., Int. Ed. 2008, 47, 4436-4439.